Basketane

Basketane
Names
Preferred IUPAC name
Pentacyclo[4.4.0.02,5.03,8.04,7]decane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C10H12/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h3-10H,1-2H2
    Key: QKWLQWFMFQOKET-UHFFFAOYSA-N
  • InChI=1/C10H12/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h3-10H,1-2H2
    Key: QKWLQWFMFQOKET-UHFFFAOYAB
  • C2CC5C1C4C3C1C2C3C45
Properties
C10H12
Molar mass 132.206 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Basketane is a polycyclic alkane with the chemical formula C10H12. The name is taken from its structural similarity to a basket shape. Basketane was first synthesized in 1966, independently[1] by Masamune[2] and Dauben and Whalen.[3] A patent application published in 1988 used basketane, which is a hydrocarbon, as a source material in doping thin diamond layers because of the molecule's high vapor pressure, carbon ring structure, and fewer hydrogen-to-carbon bond ratio.[4]

  1. ^ Marchand, A. P. (1989). "Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes". Chem. Rev. 89 (5): 1011–1033. doi:10.1021/cr00095a004.
  2. ^ Masamune, S.; Cuts, H.; Hogben, M. G. (1966). "Strained systems. VII. Pentacyclo[4.2.2.02,5.03,8.04,7]deca-9-ene, basketene". Tetrahedron Lett. 7 (10): 1017–1021. doi:10.1016/S0040-4039(00)70232-2.
  3. ^ Dauben, W. G.; Whalen, D. L. (1966). "Pentacyclo[4.4.0.02,5.03,8.04,7]decane and pentacyclo[4.3.0.02,5.03,8.04,7]nonane". Tetrahedron Lett. 7 (31): 3743–3750. doi:10.1016/S0040-4039(01)99958-7.
  4. ^ WO 1988002792, Pastor, Ricardo C., "Process for depositing layers of diamond", published 1988-04-21, assigned to Hughes Aircraft Co. , since withdrawn.